Potent inhibitor of PLD1 and PLD2
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FIPI

Item No. 13563

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl]-5-fluoro-1H-indole-2-carboxamide
CAS Number
939055-18-2
Synonyms
  • 5-Fluoro-2-Indolyl des-Chlorohalopemide
Molecular Formula
C23H24FN5O2
Formula Weight
421.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:9): 0.1 mg/mlDMSO: 20 mg/mlEthanol: 0.25 mg/ml
λmax
288 nm
SMILES
O=C(C1=CC2=C(C=CC(F)=C2)N1)NCCN3CCC(N4C(NC5=C4C=CC=C5)=O)CC3
InChi Code
InChI=1S/C23H24FN5O2/c24-16-5-6-18-15(13-16)14-20(26-18)22(30)25-9-12-28-10-7-17(8-11-28)29-21-4-2-1-3-19(21)27-23(29)31/h1-6,13-14,17,26H,7-12H2,(H,25,30)(H,27,31)
InChi Key
LHABRXRGDLASIH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $143

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    10 mg

    $259

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    25 mg

    $587

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    Product Description

    Isoforms of phospholipase D (PLD) cleave the head group from phospholipids, releasing the second messenger phosphatidic acid (PA), which can produce changes in Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. FIPI is a derivative of halopemide which potently inhibits both PLD1 (IC50 = 25 nM) and PLD2 (IC50 = 20 nM).1,2 It also prevents PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis.1 FIPI has good pharmacokinetic parameters in rats, with a half-life greater than five hours, a Cmax that, at 363 nM, is greater than 10-fold the IC50 versus PLD2, and bioavailability of 18%.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Su, W., Yeku, O., Olepu, S., et al. 5-fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis. Mol. Pharmacol. 75(3), 437-446 (2009).

    2. Monovich, L., Mugrage, B., Quadros, E., et al. Optimization of halopemide for phospholipase D2 inhibition. Bioorg. Med. Chem. Lett. 17(8), 2310-2311 (2007).

    Product Citations

    Leis, H.J., and Windischhofer, W. Phospholipase D1 activity is crucial for cytosolic phospholipase A2 -dependent prostaglandin E2 formation in murine osteoblastic MC3T3-E1 cells. Prostaglandins Leukot. Essent. Fatty Acids 198-199, 102592 (2023).